One More Round
by OtherLuces
Summary: Dean crosses paths with a former girlfriend at a bar in Philly one evening and they spend the evening reminiscing about their relationship. (M for language and smut)


**So this a one-shot based on a request I received from a lovely Anon on tumblr. The request was Dean encountering a woman who he used to date, them catching up, him trying to turn her on and her finally caving to the sexy pressure. Sorry it took so long, my dear, but I hope you enjoy it!**

* * *

><p>"Another round?" Roman asked. A bright but relaxed smile lit up his face.<p>

"Nah man, I think I'm going to call it early tonight." Dean slowly turned his empty glass with his long fingers. Roman's brow furrowed.

"Really? You feeling alright? I've only ever seen you play with your glass like that when there's something wrong."

"No, nothing's wrong, dude. Don't worry. I just have an early flight back home in the morning and I'm tired. It's been a long week and I'm thinking I might catch some sleep while I can, you know?" He scratched at the bit of stubble that had begun to grow in and sighed. "Also being in Philly makes me kinda wistful," he mumbled.

"Why's that?"

"I lived here for a while and...I don't know...seeing the buildings and smelling the cheesesteak in the air...it kinda brings up memories from back then."

"Good memories or bad? Not that I can think of any time that the memory of cheesesteak would be bad," Roman laughed.

"Both, honestly. And they are fucking delicious, right?"

They continued to talk about the nuances of a good cheesesteak sandwich until Roman finally convinced Dean to have one more drink. Dean offered to pick up this round and headed toward the bar.

"Two glasses of JD, neat, please," he said, once he had the bartender's attention. As he pushed a $20 forward, he added, "Keep the change."

He took a seat on a stool while he waited. It was an easy order, but it was busy, so he knew it might take a minute or two. He put his head down on the bar top and closed his eyes for a moment. He felt his body relax – his shoulders had been bugging him this week – and he was about to drift off until he heard the door open and a familiar voice cut through the loud chatter. It had been almost three years since he had last heard it.

He jerked up and looked into the mirror behind the bar. Sure enough it was her. She wasn't paying attention to anyone in the bar; her entire focus was on her conversation with her friend.

"Of all the fucking gin joints..." he muttered. The bartender placed the two drinks in front of him and turned to walk away, but Dean touched his wrist. "Hey, here's another twenty...can you send the chick over there in the red cardigan a rum and coke with two cherries in it? Just tell her it's on the house."

Dean carried the two drinks back to the table where Roman was busy texting. Dean sat down and stared at his glass. He so badly wanted to glance over to the table she'd sat at across the bar that he began to feel his neck muscles twitch. He finally gave in and turned his head around to watch her, slowly rubbing his thumb over his lower lip. Roman's voice snapped him out of his haze.

"Who are you staring at?"

Deciding to not bother trying to do a song and dance around telling Roman the truth, Dean sighed and took a sip of his drink. "A memory. Good and bad." Roman arched his eyebrow at Dean, so he clarified. "Ex-girlfriend."

"Ahh," Roman nodded. "What happened? Bad break-up?"

"Not really. We were just moving in different directions. Literally. I got signed and was moving to Tampa. I asked her to come with me, but she had wanted to move to LA to try to pursue a career in acting. Neither of us wanted to deal with long-distance bullshit, so..."

"So no wonder you're shocked to see her back here." Roman rubbed his chin, staring off behind Dean, who was finally taking a long sip of his drink. Roman's eyes flicked back and forth between his phone and Dean before he picked up his own drink and finished it off. "Well uce, I'm gonna call it a night."

"What? Right after you gave me shit for wanting to call it early?"

"Yeah. I've been kinda sexting with Galina since we got here. It's about time for me to go back to the hotel and Skype with her, if you catch my drift."

"You fucking horny asshole," Dean smirked. "Yeah, fine, get out of here. Ditch me like a jerk."

Roman's eyes glanced above Dean's head as he stood up from the table. "Think of it as me tagging someone else in." He smiled and lightly slapped his hand on the table. Dean watched, confused, as his friend walked away.

"No one else knows I like cherries in my rum and coke."

He jerked his head around and looked up to see her standing there, holding her drink, and staring at him with those sad eyes he had gotten to know so well at the end.

"Angela..." he mouthed silently.

"Do you mind if I sit down?"

"Yeah, uh...sure. Go ahead." He took another sip of his drink and placed it down onto the table harder than he intended. "What about your girlfriend, though? Won't she be pissed that you left her?"

"Nah, she'll be alright," she said, sitting down. "She was actually here for a first date and she just wanted me nearby in case she needed to bail out. As long as I'm in the bar, it's fine."

"It's good to know you're still protective of your friends."

"Women have to be, or then they'll end up with guys like you."

He dropped his head and laughed, shaking it slightly. "Yeah, I suppose I deserve that. Especially the way I was back then."

"That was only, what, three or four years ago?"

"That's the perfect amount of time for people to change. To move to a different place. To surround themselves with better people. To work for what they really want out of life."

"So that's why you're this huge star now?"

"Nah, I'm nobody."

"Fuck you, I was driving down the turnpike the other day and passed a huge truck with your face plastered on the side. Nobody, my ass."

He picked up his glass and held it to his mouth. "I always liked your ass." He took a sip while she glared at him with pursed lips.

For as uncomfortable as their break-up had been, and despite the fact that they hadn't contacted each other in over three years, they were getting along surprisingly well. It was almost like nothing had ever changed. He had always been able to push her buttons, but not in a cruel or manipulative way. More in an embarrassing way. He loved to make her feel uneasy by complimenting her, although usually not in the classiest of ways.

Her tight grimace eased into a smile. "You know...it's gotten better since you last saw it."

She reached two fingers into her glass to pull out one of the cherries. She put it up to her lips and licked off some of the alcohol before sucking it into her mouth. He couldn't quite tell if she was doing this on purpose or not. Whenever they were out drinking with friends, that was her sign that she wanted to go home and fuck, but that had to just be a habit by now, right? She couldn't be implying anything...could she? He swallowed hard and quickly finished the last of his drink.

"I bet it has. I'd love to see it at the end of the night."

She raised an eyebrow at him.

"Oh shit, I mean as you leave! Like I can take a look while you get in a cab or something. No, no, I didn't mean...I wasn't...uh...sorry."

"Still not as smooth as you think you are, huh?" she laughed.

"I'm super smooth and cool, thank you very much!" he pouted, crossing his arms.

"Truthfully, I liked you best when you were kind of an idiot. You big dummy. That's how you charmed your way into my life."

They sat quietly for a minute, both thinking about how things had ended so abruptly, despite the fact that, as relationships go, theirs had been so good. Finally, Dean sighed and broke the silence.

"So you haven't mentioned why you're in Philly."

"Neither have you," she snapped back.

Dean was surprised at her reaction. "Woah, what was that for? I'm here because we had a show tonight, obviously. I have a flight back home later this morning."

"Tampa?"

"Nah, Vegas. Tampa was great, but you know how I don't like to stay in one place too long."

"Yeah..." she trailed off, picking the second cherry out of her glass and eating it quickly.

"Look Angela, I asked you to come with me and you made the decision not to. You can't still blame me after all this time? You got the courage to go pursue your own dream and that's wonderful. So are you in Philly to film something?"

He noticed her eyebrows furrow and her eyes wander to the side. It felt like she was avoiding eye contact.

"What's wrong? What happened?"

"I moved back here last year. I spent two years out in LA and I couldn't cut it. I got an agent and went on audition after audition, but the most I ever landed was a commercial for a fish market in some small town on the coast of California. Eventually my agency dropped me and I could never get another one. I waited tables the entire time I was there and eventually, I just gave up. A combination of barely being able to afford my rent and the constant rejection just killed me. I had to come home."

"I...wow. I feel like shit now."

"Why?"

"Just because things turned out really well for me and they should've turned out the same for you. I just feel bad sitting here in front of you."

"It's not like it's your fault I'm a shitty actress, Dean," she laughed. "It just wasn't something I was meant to do. You were always meant to wrestle. I'm very happy for you that you get to do what you love and it's even better that you're ridiculously successful at it."

"Thanks," he smiled. "So what are you up to now?"

"I'm actually using my degree and working with special needs children."

"No shit?"

"Yeah, go figure, right? Can't find a job around here with what I went to fucking school for, leave for two years, come back, and boom. It just falls into my lap. It's great, though. I truly feel happy and fulfilled by what I'm doing now. Legitimately."

He could tell by her body language that she was being honest. She was never really one to lie about her feelings, but when she was trying to hide something from him, she always scratched her left arm. He chuckled to himself that he still even remembered that. So many details that he thought he'd forgotten were rushing back to him as he talked to her. He'd forgotten how much he really had loved her.

"I'm proud of you, Ang." He leaned forward and put his hand on hers.

She stared at his large hand covering hers. It was warm and rough, just like it had always been. She felt a twinge of something in her stomach – butterflies, perhaps – and was afraid to look at him right then because she might do something she'd very soon regret. He started to slowly rub his thumb against her own. It was something he'd often do whenever they had cuddled, usually right before he moved in to kiss her. She took a deep breath and held it in, slowly looked up at him, fearing yet desiring what may be coming.

"Alright everyone, this is last call!" the bartender called out.

Angela breathed out in relief. She wasn't sure what was about to happen in that moment of tension, but whatever it was going to be, she was glad that it had been interrupted.

Dean leaned back in his chair and smacked his hands on the table. "One more round?"

She smiled and nodded. "Yeah."

* * *

><p>Outside of the bar, Angela said goodnight to her friend and her date as they hopped into a cab together. Things had gone well and they'd already planned for a second date. She turned back to Dean who was hanging out in the shadows, leaning against a wall.<p>

"So you should probably be getting back to your hotel, right?"

"Yeah, I suppose so. Do you wanna share a cab?"

"No, I'm just gonna walk. I don't live too far from here." The light was dim, but she could see worry creep over his face. "Would you like to walk me there? Standing next to you, no one in their right mind would try to mess with me."

"Yeah, I'd love to. I never get to really walk around the city whenever we're here."

He stepped forward into the light and she realized that this was the first time she'd been able to get a really good look at him all night. His ass seemed to fill his jeans much better than it ever had in the past and it suddenly dawned on her just how much larger he'd gotten on top. When he'd said to her that he needed to get in shape if he was ever signed by WWE, she didn't realize at the time how serious he had been.

"You've...uh...you've grown since I last saw you," she said, feeling flustered.

"Nah, still the same height." He leaned his elbow on her shoulder, making a scene over his height advantage.

"No, I meant that you've gotten bigger. Like you're in amazing shape. I kinda feel bad even standing next to you."

They began to walk down the main street before taking a left down a side one.

"That's ridiculous. You've always been beautiful and I'm like a fucking bridge troll."

She punched him in the arm. "Don't give me that. You've always been handsome and you know that. Women flock to you for a reason."

"And what reason is that?" he asked, not bothering to hide his cheeky grin.

"I'm not going to give you the pleasure of me saying it out loud. You know why."

"What can I say? I've been working hard and eating my protein. My friends at work have been helping keep me on track. You can thank them for how I look now."

"Every woman who is attracted to men is thankful. Speaking of protein though, remember that time we went to Tony Luke's and you ate six cheesesteaks in a row?" she asked, trying to hide a smile.

"You mean when they crowned me King of Cheesesteak Land?" he said with a cheeky grin. "Lucky me I didn't throw up until I was outside in the alley."

"I was actually in there the other day and they asked about you."

"No shit?"

"Yeah, since you're this big-time celebrity now, they still remember you." She lowered her head and bit her lip. "Not that it's easy to forget you."

He shoved his hands in his pockets as he watched her. He could see a flush of pink appear in her cheeks. She had always blushed so damn easily. It was one of his favorite things about her. She was easy to read, for better or worse. When he'd come home drunk and barely able to stand after hitting the bar with his friends after a show, he could still tell that she was properly pissed off and disappointed in him. Nevertheless, she always made sure that he was comfortably in bed with plenty of water and some aspirin before she headed off to work. She always took care of him when he was beaten up after some bloody deathmatch. Even during the rough times, she had always stood by him. No other woman ever had before or since.

"My apartment is just at the end of this street," she said, bringing him back to the present.

"Okay cool. So do you live alone or do you have a roommate? Friend? Boyfriend?"

"I live with my friend Sam, but she's visiting her family in Washington this week so I have the whole place to myself. It's been really nice, but it's starting to get kinda lonely." He slowly nodded his head as she spoke. "And no boyfriend. Not since I moved back here. I dated a few guys in LA, but they all ended up being those horrible stereotypical SoCal douchebags. They seemed great at first but they couldn't keep up the mirage very long. I like more down to earth guys."

"Have you wanted to date anyone since you moved back here?" he asked.

"I guess so? I don't know, I spend so much time with the kids and the last two guys I was with just put me off of dating for a while. I think now might be time to give it a try again, though. Now that you mention it."

"I hope you find someone who can make you happy."

"Yeah that'd be nice, but right now all I really want is someone who can fuck me senseless. It's been a very long time."

"Good to know," he laughed.

She covered her face in horror as she realized what she'd said. "Oh my gosh, I didn't just say that out loud!"

"Oh yeah you did..."

"Nooo! Just forget I ever said anything!" Her face felt like it was on fire.

"Nope! I heard that one and I'm keeping it all to myself."

She punched him in the arm and he staggered back, feigning injury. They both laughed as they reached their destination. He waited at the bottom of the stairs as she went up to unlock her door. He watched the way her ass moved as she climbed each step. She hadn't just been bragging. Her ass really had gotten better. He felt his cock twitch and he bit the inside of his cheek to try to stop the thoughts that had begun to fill his head. This was not the time or place for such things.

Once she was all set, she turned around and smiled. She wasn't sure what an appropriate goodbye would be. They had not seen each other in years, but they had been so close at one time. Just a wave and a goodnight felt too distant, yet a hug might be too intimate? She hesitated as she tried to decide how to act. Dean walked up the stairs toward her once he noticed that she had frozen.

"It was really great to see you again, Angela. I had intended to make it an early night, but I'm glad that I didn't."

"Yeah. I'm glad, too. Thanks for the drink, by the way. I never formally thanked you."

"It was nothing. Really."

They stood facing each other, fidgeting in silence. She decided to go in for a hug. The mix of alcohol and loneliness she had felt all week was making her crave human contact, so it was worth a shot. As he saw her arms open and her body lean forward, he responded in kind. Her arms wrapped around his waist and his pulled her close to him. It felt familiar and comforting. For a moment, they were both lost in the feeling of each other and it was like the last three years never happened. He was caught in the moment and impulsively brought his mouth to her neck and kissed it softly like he had so many times before. The gentle touch of his lips and the heat of his breath on her neck made her body feel warm despite the chilly night air. Her eyes closed and her lips parted as a soft moan fell from her mouth.

They both jerked back, breaking the embrace. Her face was bright red and she even noticed some color in his cheeks as well.

"Sorry about that, I shouldn't have...uh...I'm just gonna go," he stuttered.

When he turned to leave, she reached out and grabbed his wrist.

"Wait," she blurted out. He looked down at her hand and his eyes slowly traveled up her arm, back to her face. "Would you wanna crash here for a bit?" she said after a pause. Her brown eyes were heavy and dark as she bit her lip, waiting for his response.

He lowered his head as his lips slowly curled into a smirk."Would you have a bed for me?" he asked, eyeing her through his lashes. The only response she could give was a small nod.

The apartment was dimly lit by the light from the street. She didn't bother to turn the lights on as she lead him down the hallway, and finally stopped between two doors.

"This is my room here and that one is my roommate's. You could use hers...if you want..." Her voice trailed off as he shook his head.

"I don't want that. I want you."

She lunged forward and cupped his face in her hands as her lips pressed against his. The stubble on his face prickled against her palms as she stroked his cheeks. He grabbed her hips and squeezed, slipping his tongue into her mouth. She jumped up and wrapped her legs around his waist. She felt around for her doorknob behind her and turned it as he pushed forward and they stumbled inside her bedroom.

He regained his balance as he headed toward her bed. He lowered her down onto her back and made quick work of unbuttoning her pants.

"I'm kicking myself for not wearing a skirt tonight," she groaned as he pulled off her pants and panties.

"It would've made things easier, but I've always enjoyed a challenge," he said, lightly biting down on the flesh of her bare hip.

He spread her thighs with his hands and kissed his way up her inner thighs until he reached her warm pussy. He lightly brushed his nose against her lips, feeling some of her wetness get on his skin. He could smell how strong her arousal was. He rubbed a long finger between her lips, coating it with her fluids. Given how wet she was, she must've been thinking about this since they were at the bar.

"You smell as good as I remember," he said. There was enough light coming into the room from the windows that she could see him kneeling between her legs. She groaned and curled her toes as she watched him take his finger and stick it in his mouth, sucking it clean. "Tastes even better," he grinned.

She watched him slowly lower his mouth down to her pussy and she arched her back when she felt his tongue slip between her lips and slowly circle against her clit. He rubbed the sides of her thighs while he let the taste and the feel of her wash over him. She began to moan, the volume escalating quite fast, and before Dean knew it, her hands were on his head, holding him down as she came. He gently lapped at her clit as she came down, a few extra spasms here and there making her body twitch. She relaxed her grip on his head and he came up for air.

"That was fucking quick," he laughed.

"No shit, Dean. I told you it's been a while."

"Apparen-" He was cut off by her mouth covering his as she began to pull his shirt up and over his head.

"Take your pants off," she said, taking a moment to admire his muscular frame. She bit her lip hard and felt her face flush when she took in the sight of him completely naked. He'd always looked great, but now... She wasn't a religious woman, but she felt like she should be thanking some sort of deity.

"You alright there?" he asked. She could see the cocky smirk on his face. He knew _exactly_ what he was doing to her.

"Yeah. I'm good." She grabbed his arm and pulled him down onto the bed, pushing him onto his back and straddling his hips. She reached behind her and stroked his cock a few times before a look of disappointment crossed her face. "Uh...I don't have any condoms..."

He waved his hand and made one appear between his fingers. "I took one out of my wallet while you were hypnotized by me."

She lightly slapped his chest and grabbed the packet from him, tearing it open with her teeth and rolling it on for him. She grabbed his cock and held it up so she could sink her body onto it. She whimpered as she felt him stretch her out. She knew that she had wanted this bad, but she hadn't realized just how badly her body needed it, too.

"Fuck, I forgot how good you felt. You're so damn tight," he moaned.

She rocked her hips back and forth and rubbed her hands along his stomach. "You're pretty tight yourself these days," she grinned.

"I took my shirt off when you told me to...so now I want you to take your shirt off."

She crossed her arms and grabbed the bottom hem of her shirt, pulling it up over her head and letting it drop behind her.

"You are so fucking beautiful," he whispered. He rubbed his hands up her waist to her chest, cupping her breasts and teasing her nipples with his thumbs. When he felt them finally harden under his touch, he gave them a playful pinch before he dropped his hands to her hips and helped guide her pussy up and down his cock.

She took over playing with her breasts, massaging them and rolling her nipples between her fingers. He watched her ride his cock and relished in how much she was enjoying herself. Her eyes were shut and her head was tilted back. The sound of soft moans and heavy breathing filled the room. He watched her fuck herself on his dick for as long as he could, before he couldn't take it anymore and wanted to make her cum himself

He growled at her and grabbed at her shoulders, rolling her over onto her back. She wrapped her legs tightly around his narrow waist, holding on for dear life as he thrust in, hard and deep. He pinned one of her wrists above her head and lowered his face into her neck. He nipped at her skin, leaving tiny red bite marks. His other hand slid down her stomach until it stopped at her pussy. He rubbed her clit gently with his thumb and by the way her thighs were squeezing him, he knew that he was receiving the desired reaction.

Her moans got louder and she began to claw at his back with her free hand. She felt a second orgasm building inside of her, just aching to burst forth.

"Cum for me, Angela. I want to feel you cum on my dick."

His raspy voice coaxing her to orgasm actually helped her over the edge and she cried out as she came, quickly biting into his shoulder to quiet herself out of habit. He felt her pussy clench around him and it was too much. With a few last stiff thrusts, he came as well.

She felt a bead of his sweat drip down onto her cheek as she looked up at his face. His eyes were narrow, but not completely closed, and his mouth was open. A loud groan was rumbling from his throat. He held himself above her, his body stiff, and she could feel his cock pulsing inside of her. She lifted her free arm up and draped it around his neck, pulling his body down on top of her and feeling the warmth of his lips against hers. She wished that she could freeze this moment and savor the sensation of his weight on top of her.

"I should go deal with the condom," he mumbled into her mouth.

"Yeah...I guess you're right," she reluctantly agreed.

He kissed her forehead and pulled out of her, rolling off to the side and onto his feet. He stopped in the doorway and glanced behind at her. "Which side of the hall is the bathroom on?" She pointed to the left and he gave her a wink and a thumbs up. She turned onto her side and giggled. It was good to know that he was still a dork at heart.

When he returned to her room, she was already asleep. He chuckled to himself. "Some things never change," he whispered as he climbed back under the covers with her.

She rolled over and snuggled up against his chest once his weight had settled next to hers. It wasn't a gesture out of affection, it seemed, as much as a reflex to there being another warm body. Still, the sight of her lying next to him - her hair messy, her breathing slow and even – got to him. It felt like he had just woken up and they had never broken up. Neither of them had walked away from each other as they pursued their own dreams. A little piece of him wished that that was the case. He wrapped an arm around her upper back and stroked her hair. Maybe long distance wouldn't have been so bad.

He kept his eyes open while he waited for the time before his flight to tick away. If he had closed his eyes, he surely would have fallen asleep and he didn't want to have to set an alarm and possibly wake her up before he left. He didn't mind, though. He was perfectly happy watching her sleep.

When it was time to go, he carefully got out of her bed and threw on his clothes. As he was about to leave the room, he heard her voice faintly behind him.

"Mm...Dean...don't go..."

He turned around and saw that she was still asleep. Had she spoken in her sleep or had he imagined it? He made a quick decision and walked over to her desk, quietly looking for a pen and a piece of paper. He scribbled down his name and phone number and placed the note on the bed where he'd been lying.

He leaned over and pushed her hair out of her eyes, a small smile lighting his face. "Thank you for tonight, Angela," he whispered, unsure whether or not she'd hear him through her sleep. "I hate having to leave you again. But if you ever want to try one more round, you've got my number."

He kissed her on the lips and when he pulled back, he noticed that she was smiling. He headed out of her bedroom and softly closed the door. Once he was outside, he inhaled deeply, smelling the early morning air. He noticed that the sky was beginning to lighten and he smiled to himself. It felt like it was going to be a good day.


End file.
